She Need My Sissy Maid Service👰‍♀️🎀Part 4(Crossdressing Stories)

Hey everyone, welcome to M2F story. Today I am going to share with you serving as made part 4 written by Carolyn. So if you are new to the channel then please consider subscribing and check out my Patreon patreon.

com/m2f story. I'm truly sorry if I've offended you by allowing you to think I'm a woman, Gary. I've been having such a grand time doing this that I'm afraid I lost sight of how I might hurt someone.

You know, Caroline, I am surprisingly not upset with you at all. I must tell you, the news comes as a complete shock to me. I'm sure you realize how what an attractive woman you make.

Your sense of style is wonderful. Your makeup is perfect, and you have lovely hair. However, it is your personality that makes you the woman you appear to be.

It's obvious now that I know the truth that you really have gotten into the role. I'm glad you told me, but even now it is hard to interact with you without feeling like I'm talking with a woman. Oh, Gary, that is the nicest thing to say.

I'm so happy you can accept me as I am. We talked for over an hour before Gary realized how late it had become. As we prepared to leave, he asked for my phone number.

I'd like to call you, Carolyn. I've had no one to open up to for such a long time, and I feel we really connected. Strange as it may seem, I'd like to see you again.

I feel the same way, Gary. I'm very comfortable with you and truly enjoy your company. I hope you call me.

As I drove away, my thoughts remained on this new man in my life. He and I truly had quite a bit in common. We certainly talked easily with each other.

Suddenly, I was afraid he may not call me. I ran a few errands. I decided to pick up a sweater set to wear to Anna's for the pre-party preparation.

I also bought a pair of red flats. I never had any woman's shoes other than heels and thought for my work the next day. Flats would be appropriate.

When I got home, there was a message from Gary. How exciting. I returned the call at once.

Hi, Gary. I'm so sorry I missed your call. I was shopping after our lunch.

Hello, Carolyn. I'm glad you called back. I just wanted to tell you how great it was to meet you and spend time with you today.

I definitely would like to see you again. Will you have dinner with me? Yes, I replied.

probably a little too quickly. When would you like to meet? I know you are working Saturday night, so how about tomorrow?

I hope I'm not being too forward, but I really want to see you soon. I feel liberated from my self-centered sadness and have you to thank for it. Saturday will be wonderful.

I am working that day preparing for the party, but I should be home by 5 now. Super. I'll pick you up at 7.

Okay, I'll make reservations. Just give me your address and it's a date. I gave him the address and we rang off.

I was almost giddy with excitement. This surprised me and I sat down to digest what had happened. After months of solitude, I suddenly had a new friend that accepted me as the woman I had become.

Further, my friend was a charming man who had sorrows of his own. We certainly fed off each other in such positive ways. I tried to rationalize that it was just a friendship that we were beginning to nurture.

The more I thought it through, the more I realized I was curious about what the nature of our relationship might become. Did I want him to kiss me? I hadn't been kissed for over a year.

Did I want to kiss him? I know he had not had any intimacy for 3 years. What a delicious predicament.

It shook me as I realized that yes, I did want his lips on mine. I had never been kissed by a man before. I had no idea how it would feel or even if I would enjoy it.

However, I knew that thinking about it was exciting. I would have to tone down my emotions at dinner. My goodness, who would have guessed that this subservient maid would harbor such aggressive thoughts?

The more I delved into womanhood, the more curious the experience had become. Today had been a day of revelation. Perhaps it began with my fantasy watching a woman being kissed in a movie.

or maybe somewhere deep in my heart. This curiosity had been brewing for months as I hid my sadness behind dresses and heels. As I spent the remainder of the day cleaning and getting ready for bed, thoughts of Gary were never more than a blink away.

I decided to find another old movie with a beautiful heroin I could become in my mind. Sure enough, a kiss scene came and after watching it, I closed my eyes and pictured me and Gary in the pose. Then and there, I knew I wanted him to hold me.

Oh my. How to deal with this? Friday morning I awoke with energy.

It was a good thing since today I was going to help prepare for Anna's party. I showered, shaved, and prepared to dress. I wore my new breasts, of course, along with my gaff.

I knew I was going to be working hard, so I chose a loose- fitting blouse and a kneelength skirt that wasn't too tight. Prior to dressing, I remembered that my nails were only allowed a touch of color. The bright red on them now would not do.

I cleaned them and applied a pale rose that I hoped wouldn't offend. I just couldn't bring myself to not having any color at all. That task completed, I put on a slip and added the blouse.

I chose a pair of panty hose and then stepped into my skirt. Finally, I selected a pair of red flats that would allow me to work quickly and be easy on my feet. After slipping them on and standing, I realized how long it had been since I had not worn heels.

I missed them immediately, but realized that this was a job, not a fashion show. Adding some conservative makeup with just a touch of pale rose lipstick, I was ready to go to work. Grabbing my purse, I walked slowly to the car.

I realized that without heels to remind me, I would have to be alert to the fact that I was not just a guy in woman's clothing, but a man who was portraying a woman's role. As far as Anna knew, I was the woman whom she met at Mark and Mary's party. the woman who provided such subservient yet professionalmade services.

It was quite a joy to be in this role. When I arrived, another girl was there. She had already begun the preparation.

After introducing ourselves, we dug in and worked quite well as a team. Within a few hours, our jobs were done and we were ready to leave. Anna came to inspect and was totally satisfied with what she saw.

You ladies did a fine job. Caroline, I am very pleased to have discovered you. It appears you take pride in your work and are not one of the many ostentatious women my agency has tried to saddle me with.

I don't understand why so many of the girls that are assigned here feel the necessity to wear revealing clothing and horish makeup. Thank you for paying attention to my rules. It is my pleasure, ma'am.

I am so happy for the opportunity to work for you both today and tomorrow. I hope you'll be happy with my service and allow me another chance in the future. As for your rules, I find them quite logical.

I'm not here to impress anyone with my clothing or style. My job is to serve you and your guests in the manner you expect. She really seemed to like that response.

I was a bit surprised at myself. I normally would never reply in such a passive manner. In fact, it seemed to me that I was being a bit submissive in my answer.

Of course, that was what she wanted to hear, but instead of phrasing my comment to meet her expectations, I actually meant what I said. I had certainly accepted my role as a servant, and frankly, I enjoyed my status. It dawned on me that I enjoyed it because my status was entirely female in her eyes.

How nice it was to be accepted in such a role. We left shortly thereafter, and I buzzed home, my mind fully focused on my dinner date with Gary. While I did not expect it to be anything more than a let's get to know each other evening, deep in my heart I had to admit that fantasies were spinning.

When I arrived home, it was barely too sour. I had a full 5 hours to prepare. My thoughts leapt to what I would wear.

Should I try to dress provocatively? My goodness, I had never thought that way before. What a silly girl.

I didn't have clothes that were designed for enticing a man. My entire wardrobe, aside from my working woman attire, was selected for me. I enjoyed dressing and acting as a woman, but until last week, never with an eye for how my attire would affect anyone's opinion of me.

All I cared about up to now, was that I was accepted as a woman. This line of thought gave me serious pause. What in the world was I going to do to balance these new emotions against my realistic understanding of whom and what I really was?

I decided a nice hot bath would help me relax and focus on the evening ahead. As I soaked, it dawned on me that tonight was not a make orb break date. Yippy, I was going on a date.

No, this was merely an evening to spend with a very sad and needy man who I assumed was looking to me to become a friend with no strings to the past. As I pondered this, I realized that indeed I would be thrilled to play such a role in a person's life. Actually, I could use a friend with no ties to my past as well.

A fresh start would likely be beneficial to both of us. When I had climbed out of the bath and towelled dry, I applied scented lotion and started on my hair. I still was waffling between a flip outward and the inward flip that I had worn the last few days.

I decided on the inward style as I enjoyed the way it framed my face. I wasn't unhappy with my hair color, although I realized that it wasn't vibrant at all, just a plain brunette. Perhaps I should look into some highlights.

I also did not want to wear pale nails tonight. While I didn't want to try to look like I was on the make, as it were, I certainly felt that a brighter color would be appropriate. Before choosing the hue for the evening, I deemed it wise to decide what to wear.

After all, no sense in sporting nails that clashed with my outfit. I had been thinking about a plain black dress I had acquired a few months prior. It was short-sleeved and before cleaning the hair off my arms, I had never really enjoyed wearing it.

Now that my arms were femininely barereft of hair, it would be a great selection. I had saved most of my late wife's accessories. Her clothes didn't fit well, and I had given them to our thrift shop.

However, all of her jewelry, purses, and scarves were still neatly tucked into drawers. She had a beautiful silk shaw, what would be a colorful accent to my dress. It was full-sized and had a mix of pastels in its design.

The overall theme was pink with soft yellow and blue accents. I laid it out on the bed and pulled a few nail polish bottles out. I finally decided on a fairly bright pink that matched the shaw nicely.

This, of course, would set the tone for the rest of my makeup. I gave thought to wearing stockings, but decided that panty hose would be more appropriate. Frankly, stockings gave me chills, not only as I put them on, but usually unexpectedly as I wore them for a period of time.

They were quite feminine, if not flatout sexy feeling. I did wear a corsellet over my gaff, and after tucking in my breasts, I put on a full black slip. It didn't matter if I needed a slip or not, I loved them and wore one nearly everyday.

I slipped on my panty hose, having selected a sheer black pair that would work well with my dress. I had obtained a pair of strappy 3-in heels that I simply adored. As I put them on, I reveled in the slinkiness they added to my look.

Finally, I stepped into my dress. It zipped up the back, and it clung to my body quite nicely. I went to the mirror and loved what I saw.

I added a simple necklace with a small black stone that hung just to my cleavage. I thought dangling earrings wouldn't be too garish, and they were perfect. A pair of gold bracelets on my left arm along with a gold ring on my right hand seemed to balance the outfit well.

I put the shawl over my shoulders and it fell gracefully over my breasts. Frankly, I had to admit I looked pretty good. All that was left was my makeup.

I took off the shawl and applied foundation and cover up. I decided to add just a hint of pink toner and selected a pale pink eyeshadow. After lining my eyes and applying mascara, I brushed on the eyeshadow and was thrilled with the image.

I used a tube of pink lipstick and added some pink gloss on top. Smacking my lips, I shivered with delight at the taste and feel of them. If men only knew what they were missing.

Lipstick is the most sensual part of the entire makeup routine. I stepped to the mirror again and dawned my shawl. I was quite satisfied with my appearance.

I hoped that Gary would be. It was nearly 7 and I sensed he likely would be on time. I spritzed on some perfume and selected a purse for the night.

It was a small bag but had room for necessities. Lipstick and gloss perfume, mints and my keys. As I waited for Gary, I forced myself to calm down.

The process of dressing this time for a date had excited me. I couldn't help but hope that Gary was attracted to me as I had really worked hard to be as pretty as I could be. I had to remember that we were just friends and that our dinner was likely nothing more than adding to the foundation of that friendship.

However, a girl can dream, right? When the doorbell rang, I jumped. I had been miles away in my mind, pondering all the possibilities.

Suddenly, here he was. When I answered the door, Gary took a long look at me and whistled softly. Oh my, what a shiver charged up my back.

Carolyn, my goodness, you look stunning. Why, thank you, dear. I'm so glad you think so.

He smiled and offered me his arm as we walked to his car. I clutched it rather tightly. I had never held a man's arm before.

It felt incredibly good. He opened the car door for me and I demurely sat and swung my legs in together. As I waited for him to walk around the car, my mind was flying.

It felt wonderful to be out with a man. I felt entirely female and allowed myself to luxuriate in the role. Gary entered the car and we began our drive to the restaurant.

I hope you like basic food, Caroline. I've picked a spot I used to enjoy, but I haven't been there in a few years. It used to be comfortably predictable, but I have no idea what they'll be offering tonight.

No problem, Gary. I am just so happy to be having dinner together. I certainly enjoyed meeting and talking with you.

I hope we can build on what we've started. Thank you, Carolyn. I liked our talk as well and certainly have grown fond of you already.

You're not like other women. With that, he blushed. Don't worry, dear.

I know what you meant. Of course, I'm not. But that won't matter tonight.

You make me feel 100% girl through and through. That's one of the things I like about you. We both laughed off his minor fauxaw.

Inwardly, I was entirely pleased that he saw me in comparison to other women. I was growing very interested in this man. When we arrived at the restaurant, Gary helped me from the car and I held his arm as we walked in.

No heads turned in the room. I suppose most women would be disappointed, but not this girl. I loved being accepted as the woman on Gary's arm.

Frankly, the only head I cared to turn was his. We sat and ordered some wine. The menu was perfect.

Steak, seafood, and pastas. I ordered a baked halibet dish, and Gary chose a T-bone steak. I have to tell you, Caroline, that I was pretty nervous today.

I couldn't believe that I had the nerve to call you and to make this date. It has been a long time since I've had the courage to do this. I still don't know why I did it, but as of right now, I'm very happy to be here with you.

Oh, Gary, I responded. I'm happy, too. You and I have spent too many months, in your case, years, in solitude.

It has done me a world of good to prepare to go out with you tonight. I was nervous today as well, but you certainly have calmed me down. You are a lovely evening companion.

We continued to chat while we enjoyed our dinner. The food was lovely, but the companionship was so much more than I had dared hope. Gary was a great talker once he got going.

We stayed away from our sad pasts and focused on the present. Before long, it was time to leave. Caroline, I hope I haven't bored you tonight.

I really enjoy being with you and hope we can do this again. Bored me? I replied.

Oh my goodness, Gary. This evening has been wonderful for me. I hate to see it end.

Me too, Gary continued. I haven't felt this relaxed and comfortable with anyone for such a long time. You are great therapy for me, not to mention a wonderful dinner date.

As we walked to the car, Gary took my hand instead of offering his arm. I wallowed in the wonderfulness of the gesture. Drving home, I decided to take a bold step.

I've enjoyed this time with you, Gary. Would you consider me too forward to invite you in for a night cap? It still is early, you know.

Gary paused and I could have kicked myself. You blew it, girl. I thought to myself, I was going to ask you if you wanted to stop for a drink, Carolyn.

I'd love to come in for one at your place if you don't mind. I agree with you. This night has been too nice to let it end this early.

I reached over and squeezed his hand. I'm so glad, Gary. I truly love being with you.

When we got to my house, he gallantly opened my door and asked for the house keys. Holding my hand, he led me to my door, unlocked it, and stepped back for me to enter. As I turned on the light, I turned to him, and we collided.

I didn't realize how closely he was standing behind me. Our faces were so close, I could smell his aftershave. I looked up at him and he down to me.

Without thinking, our lips met ever so briefly. It was my first kiss from a man, and I nearly swooned. I grabbed onto his arms just to catch my balance.

"Gary, I'm so sorry. You just caught me off guard and took my breath away. " He backed off apologetically.

"I am the one to apologize," he said. "I shouldn't have done that, Caroline. You just looked so kissable, and I'm afraid it just happened.

" "Gary, don't misunderstand. I loved it. Please do it again.

" He took my arms and pulled me to him. This time, the kiss wasn't spontaneous, but it wasn't any less thrilling. His lips pressed to mine for minutes, so it seemed.

Finally, we broke apart. Gary, I've thought about this very minute since the day I met you. You know about me.

Are you sure you're comfortable with such intimacy with a man in woman's clothing? Carolyn, I have been forcing myself to remember you are a man all night long. You look entirely female.

You act like a woman, and you have a definite female personality. I'm afraid I view you as a woman wearing woman's clothing. As for kissing you, it's been on my mind for days as well.

That's it for today. Hope you have enjoyed it. If you do, then be sure to subscribe for the next part of this story and show your support on Patreon.